


A Very Sissy Halloween

by orphan_account



Category: Original Work
Genre: Forced Feminization, Hypnosis, M/M, sissification
Language: English
Status: Completed
Published: 2020-10-25
Updated: 2020-10-25
Packaged: 2021-03-09 04:09:08
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,241
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27197626
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Kudos: 15





	A Very Sissy Halloween

It was 4 weeks before Halloween, and 7-year-old Callie was on the road to revenge. For too long, her older brother Peter had tormented her, making fun of her girly room and clothes, calling her the "prissiest princess," and overall being an ass. But that was what big brothers did, and it was normal. Until Peter crossed a line. He had ruined her favorite dress in the wash, a gift from her now gone grandmother. The jerk hadn't even had the decency to look sorry about it. The final straw. Callie was ready for revenge, and this was the perfect opportunity. It was time she got the 'little' sister she had always wanted.  
Her parents were going to be gone for 5 weeks, on a lengthy business trip to Japan. Peter, 17, was placed in charge and was given some money to take care of him and his sister. Callie had a friend, Sophia, who had taught her hypnosis and had proven it to her by practicing on Sophia's little brother. Over a few months, Callie had mastered the art, and now it was time to put her training to use. She mixed up some of her subtle hypnosis videos in with Peter's music, and it was nearly indistinguishable.  
She knew Peter used his music to lull him to sleep, so it was only a matter of time. After a few days of the subtle voices making his mind more susceptible, it was time to try it out. She whispered to him while he slept, "You have a deep desire to become more feminine. Any time you see nail polish, lacy socks, or panties, you have an unbeatable urge to apply them or put them on. You will do so, and be ashamed of it. You can't fight this, it's who you are mean to be."  
The next morning, Peter woke up and started to do his normal morning routine. In his bathroom, he found a small tube of glittery pink nail polish on his counter. Without much thought, he started to apply it to his nail and toenails. When he was done, he grimaced at his girly digits. 'Why the fuck did I do that?' he thought. But he continued to go about his day and started to get dressed. By his dresser, he saw a pair of pink socks with lacy ruffles at the top. 'Must be Callie's.' He thought, but pulled them on anyway, the lacy socks coming up midcalf. He did the same with the frilly pink panties he found beside the socks, the frilly pink bow looking comically girl above his obvious member. He looked at himself in the mirror and narrowed his eyes. Why was he doing this again? 

Halloween grew closer and closer, and as the days passed, Callie began to incorporate more and more girly things into Peter's wardrobe. Girly hair clips, shirts made for women, girls jeans. His friends at school were starting to notice, but Peter couldn't seem to force himself to stop. He started becoming more emptional too, crying easily, and his manners improved. To his horror, a few days before Halloween, he even developed a girly lisp that made him sound like a toddler.  
Finally, on the morning of Halloween, Callie convinced him to take her to the mall, because he was in desperate need of a haircut. It was true, his blond locks were now shoulder-length, and he needed them way shorter for his Luke Skywalker costume. He agreed to drive them, but only for the haircut. Callie had smiled.  
They arrived at the mall, but instead of going to his usual barber, he could only follow uselessly behind Callie as they headed towards a girly looking solan. Callie went to the front desk while Peter waited submissively behind. "he's here for Tina," Callie said and looked back at Peter. "Behave." Peter was led to one of the chairs in the back, and a stern-looking lady started to mess with his hair, without even asking what he wanted done. But Peter couldn't say anything. Behave.  
She wouldn't let him look as she finished, and started to apply stuff to his face. Peter desperately wanted to tell her to stop, but Behave rang in his mind. He could only sit passively as she worked. When she finally finished, he was horrified. Instead of a short boyish style he had wanted, his blond hair was tied up in sissy pigtails, perfectly done in huge sausage curls. Bright pink ribbon bows held them in place, with little jingle bells sewn into the front. But his face was even worse.  
His blue eyes had been enhanced by liner, and pastel pink shadow covered his lids. Fake lashes had been applied, and his eyebrows had been neatened up. His lips were a soft pink, and a layer of gloss made them extra shiny. An insane amount of pink blush covered his cheks, almost in perfect circles. A small pink heart sat under his left eye as if to just take it one step too far. Callie came over from the waiting room and beamed.  
"Peter, what do we tell the nice lady for making you look so beautiful?" She asked.  
Peter gulped, and in his sissy lisp, he replied, "I love it tho muth, thank you!! I'm the prettietht thiththy ever!!" and then proceeded to giggle, something he had never in his life done before. Peter felt sick. What was going on?  
Callie grabbed his hand, and after paying with their parent's card, they left the solan. Instead of returning home as Peter had instead, Callie took him to a nail tech a few stores over. Instead of his gritty chipped pink nails, he now had 1-inch long pastel nails, complete with little heart details. Then they entered a women's underwear store, where Peter was fitted with some lacy pink panties, a garter belt, and a pink bralette. The ladies in the store giggle at his reddened face.  
"He's coming out as a sissy," Callie had told them, "He's debuting on Halloween. Tell them how excited you are!" Peter forced out that he was incredibly excited to be his 'true self', and the store women giggled at his girl lisp.  
He was starting to get even more stares at the mall, and when they finally entered what Callie said would be their last store, he was relieved. Until he saw it was a costume store. She pulled him along to the back of the store, and he was horrified. It was full of adult size outfits for little girls, frilly and lacy, a wave of pinks, blues, yellows, and purples. She grabbed a package from the shelf and told him to go put it on while she found him some shoes.  
He entered the dressing room, and pulled out a large pink dress, with an attached tulle petticoat. It was short enough that if he bent over, his panties would be exposed to the world. It was pale pink, with a bright pink detail ruffle on the edge of the skirt, and pink bows spread out on the rim. The attached bodice emphasized his flat chest and had a large pink heart in the center. A pink ribbon went around his waist with an attached frilly white apron, and the puffy pink sleeves went over his pale shoulders. He tied a pink ribbon around his neck, with the bow going behind his head, and a bell was sewn into the front. Pink fingerless gloves slid over his hands, and a ribbon tied them around his wrists. His lacy pink socks fit the outfit perfectly.  
Callie slid him some pink high heels under the curtain, and he put them on. They were adorned with a pink bow placed over the toe, with yet another bell was sewn in. When he stepped out of the dressing room, Callie squealed. He felt a tear slip down his cheek. Why was this happening to him? 

They paid for the costume, with Peter wearing it out, and proceeded to drive home. When they got back to the house, Callie led him to the couch in the living room and sat him down. "You may be wondering what's going on," She said, looking at him thoughtfully. Peter nodded.  
"Well, I've decided I don't really want a brother anymore. You've never been really nice to me, and I think you are far better suited as a little sister. After tonight, when the clock strikes 12, you'll be a lovely little sissy sister forever." Peter could only sit and cry.  
"Why are you doing thith to me? I don't want to be a thithy!" He cried out, tears filling his eyes. Callie sighed and cupped his cheek. "I know." she paused, "But you will soon."  
"After tonight, will be the perfect little sissy forever. You'll smile, and flounce around in your little sissy walk," She smiled, picturing it. "Your favorite color will be pink. You'll love tea parties, doing your makeup, being the most beautiful sissy in the world. You won't need to be smart, because being sissy will be a full-time job. You can forget any brains you had, and just focus on being pretty. When you're old enough, you'll find a handsome man that loves you, and you'll get married at a big lavish wedding and a beautiful pink wedding dress. You'll be sensitive and obedient. You'll always do whatever me and mom and dad say. You'll obey your future husband as every good wife should do." Peter was about to start sobbing. "We are going to go to a Halloween party tonight, and you're going to be a perfect little sissy boy. Tomorrow, we'll redecorate your room and go shopping for new clothes. Your old boy ones aren't nearly good enough. Maybe we'll get you lip fillers! And when mom and dad get home in a week, you're going to tell them you've always wanted to be a sissy, and you're finally going to be your true self. Peter is gone, you're new name is Prissy."  
Callie smiled and clicked her fingers together. The change was instantaneous. Peter's eyes lit up, and his mouth formed a silly sissy grin. "OMG!" He squealed, "We have to get you ready for Halloween! Thereth going to be tho many cute boyth! Oh, I hope thomeone kiththeth me!" He grabbed Callies's hands and they skipped upstairs to get ready for the party. Peter was gone. There was only Prissy now. 

EXTRA:  
The party when fantastically. Prissy kissed a hunky vampire named Jace, who was totally into his whole sissy thing. They got lots of candy, Prissy got a few slaps on her rear, which she giggled at, and the night was amazing. He felt a little weird at midnight, like something finalizing had occurred, but continued to party.  
The next day, true to her word, Callie hired some people to come to redo Prissy's room. Gone were his green walls, replaced with a pretty pale pink with white trimming. A large white canopy bed with pink silk bedding filled the room. Posters with women in beautiful dresses and hunky men covered the walls. A new white dresser filled with frilly underthings sat in the corner. His closet was now filled with pretty frilly dresses of all colors and styles, with dozens of high heels sitting neatly below. A box containing jewelry and accessories sat on his new makeup vanity, waiting to be used. Callie had his ears pierced, and jangly little bells hung from his lobes. He also got luscious lip fillers, and on his back, right above his ass, he got a tattoo. In girly pink letters, the works "Prissy Sissy" were etched into his skin. He had cried like a baby, but if Callie told him to get it, he just had to. He had texted his friends and told him he was dropping out, and his new name was Prissy. All of them stopped talking to him after seeing his new Instagram. 

When their parents came home, Callie and prissy stood in front of the door to their house and greeted them. They were absolutely shocked. Prissy stood before them, dressed in his frillies clothing, and said "Mommy, Daddy, I'm a thiththy now. I've alwayth wanted to be a thiththy, and now it'th time to finally be the real me. I love the color pink, doing my hair, and being thuper pretty. Thith ith who I am now."  
His parents didn't understand, but they accepted him anyway. They were super well off, so money was never going to be an issue. If their son wanted to be some weirdo sissy boy, then who were they to say no? 

From then on, Peter dropped sports and went from being an avid football player and a member of the varsity team to a week, ditzy, frilly sissy. He learned to bake, needlepoint, and dance. Everything a good sissy wife would need to know, he learned. When he was 21, his parents arranged for him to marry Jason Stone, a well-known businessman. The wedding was huge and lavish and expensive. He walked down the aisle, his hair in a high Rocco style, with frill pink bows adorning his head. His frilly pink dress had a skirt like a ballerina and showed off his lovely panties to the wedding party. He was beautiful and splendid. Destined to be the perfect obedient sissy wife.


End file.
